Vintage 2000s Y2K Strapless Denim Dress Second Shift Vintage Chicago, IL ATTIC 2000s Denim Dress Etsy 2000s Denim Dress Etsy Canada Gen Z is bringing back dress over jeans fashion trend and millennials are reeling Vintage Denim Jean Dresses 90s & 2000s Denim Dresses The early #2000s trend of wearing dresses over jeans was a popular #y2k era look, often featuring a long dress, like a babydoll or slip dress, layered over flared or skinny jeans.